3-Chloro-N-(3-methylphenyl)benzamide

Abstract

In the mol­ecular structure of the title compound, C14H12ClNO, the meta-Cl atom in the benzoyl ring is positioned syn to the C=O bond, while the meta-methyl group in the aniline ring is positioned anti to the N—H bond. The two aromatic rings make a dihedral angle of 77.4 (1)°. In the crystal, the molecules are linked by N—H⋯O hydrogen bonds, forming C(4) chains propagating in [010].

2-Chloro-N-(3-methylphenyl)benzamide

“…E68, o723 The amide and sulfonamide moieties are the constituents of many biologically important compounds. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Bowes et al, 2003;Gowda et al, 1999Gowda et al, , 2006Rodrigues et al, 2011;Saeed et al, 2010), N-(aryl)-methanesulfonamides (Gowda et al, 2007), N-chloroarylsulfonamides (Jyothi & Gowda, 2004) and N-bromoarylsulfonamides (Usha & Gowda, 2006), in the present work, the crystal structure of 2-chloro-N-(3-methylphenyl)benzamide (I) has been determined ( Fig.1).…”

“…For studies, including ours, on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al (2003); Gowda et al (1999Gowda et al ( , 2006; Rodrigues et al (2011); Saeed et al (2010); for N-(aryl)-methanesulfonamides, see: Gowda et al (2007); for N-chloroarylamides, see: Jyothi & Gowda (2004); and for N-bromoarylsulfonamides, see: Usha & Gowda (2006). Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009) and WinGX (Farrugia, 1999).…”

3-Chloro-N-(2-methylphenyl)benzamide

“…In (I), the N-H and C=O bonds in the C-NH-C(O)-C segment are anti to each other. The meta-Cl atom in the benzoyl ring is positioned anti to the C=O bond, while the ortho-methyl group in the anilino ring is positioned syn to the N-H bond, in contrast to the syn conformation observed between the meta-Cl atom in the benzoyl ring and the C=O bond in 3-Chloro-N-(3-methylphenyl)benzamide (II) (Rodrigues et al, 2011), while the meta-methyl group in the anilino ring is positioned anti to the N-H bond. Further, the two aromatic rings are nearly coplanar with the dihedral angle of 3.48 5…”

“…For the preparation of the title compound, see: Gowda et al (2003). For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al (2003); Gowda et al (2000); Rodrigues et al (2011); Saeed et al (2010), on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004) on N-(aryl)-arylsulfonamides, see: Shetty & Gowda (2005) and on N-chloroarylamides, see: Gowda et al (1996).…”

“…E67, o3381 The amide and sulfonamide moieties are the constituents of many biologically significant compounds. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Bowes et al, 2003;Gowda et al, 2000;Rodrigues et al, 2011;Saeed et al, 2010), N-(aryl)-methanesulfonamides (Jayalakshmi & Gowda, 2004), N-(aryl)arylsulfonamides (Shetty & Gowda, 2005) and N-chloro-arylamides (Gowda et al, 1996), in the present work, the crystal structure of 3-Chloro-N-(2-methylphenyl)-benzamide (I) has been determined ( Fig.1).…”